Monk picks Mallory up at the ferry. His stepmom, Becca, was supposed to come—because Mallory has come to work as a nanny for Becca’s twins, Chippy and Blue—but Becca is hungover. Monk got her the job. She remembers one night, during college, when Monk stayed over at her mom’s. He kissed her on the lips when he left, but Mallory started dating a boy called Dillon Rooney soon after because Monk was sending her mixed messages. Monk calls her “Pinks” after a My Little Pony character, and he explains that Becca can be “difficult.” He has a rocky relationship with his father, who is a patron of the arts but doesn’t appreciate Monk’s musical talent. Monk will be on Winthrop for the summer, working as a caddy. At the house, Mallory meets Becca, then Chippy and Blue, Monk’s half-brother and -sister. That night, the kids refuse to go to bed, and Monk comes over to sing to them, and they go to sleep. After his dad and stepmom get home, he takes Mallory to Mo’s, a local pub where he performs. He introduces her to the owner, Mike, who assumes that they are a couple. Monk sings several original songs and commands the room.